Electroorganic Chemistry as a New Tool in Organic Synthesis

02.08.1984

Englisch

9783540130703

Springer Berlin

Reactivity and Structure: Concepts in Organic Chemistry

Nein

Tatsuya Shono

172

Gebundene Ausgabe

20

PNR - Physikalische Chemie PNN - Organische Chemie TDC - Industrielle Chemie und Chemietechnologie

1 Introduction.- 1.1 Inversion of Polarity of Substrates.- 1.2 Interface Reactions.- 1.2.1 Stereochemistry.- 1.2.2 Distribution of Active Species.- References.- 2 Anodic Oxidations.- 2.1 Anodic Cleavage of Aliphatic Carbon-Hydrogen Bonds and Carbon-Carbon Single Bonds.- 2.1.1 Cleavage of Carbon-Hydrogen Bonds.- 2.1.2 Cleavage of Carbon-Carbon Single Bonds.- References.- 2.2 Oxidation of Carbon-Carbon Double Bonds.- 2.2.1 Introduction.- 2.2.2 Oxidation of Simple Olefins.- 2.2.3 Oxidation of Conjugated and Nonconju- gated Dienes.- 2.2.4 Oxidation of Arylolefms.- 2.2.5 Oxidation of Enolic Olefins.- References.- 2.3 Oxidation of Alcohols, Glycols, Ethers, and Acetals.- 2.3.1 Oxidation of Alcohols.- 2.3.2 Oxidation of Glycols.- References.- 2.4 Oxidation of Compounds Containing Sulfur, Phosphorous, and Boron.- 2.4.1 Sulfur Compounds.- 2.4.2 Compounds Containing Phosphorous and Boron.- References.- 2.5 Oxidation of Organic Halides and Oxidative Halogenation of Organic Compounds.- 2.5.1 Oxidation of Organic Halides.- 2.5.2 Halogenation.- References.- 2.6 Oxidation of Aliphatic and Aromatic Amines.- 2.6.1 Oxidation of Aliphatic Amines.- 2.6.2 Oxidation of Aromatic Amines.- 2.6.3 Oxidation of Amides and Carbamates.- 2.6.4 Application of ?-Methoxy- or ?-Acetoxy- Amides or -Carbamates as Starting Materials in Organic Synthesis.- 2.6.4.1 Formation of Carbon-Carbon Bonds.- 2.6.4.2 Formation of Bonds between Carbon and Heteroatoms.- 2.6.4.3 Reactions Using ?-Methoxylated Amides and Carbamates as Masked Carbonyl Compounds.- 2.6.4.4 Formation of Enecarbamates and their Reactions.- References.- 2.7 Oxidation of Carbanions andCarboxylate Anions.- 2.7.1 Oxidation of Carbanions.- 2.7.2 Oxidation of Carboxylate Anions.- 2.7.2.1 Formation of Radicals Kolbe- Type Reactions.- 2.7.2.2 Formation of Cations.- References.- 2.8 Oxidation of Aromatic Systems.- 2.8.1 Aromatic Substitution.- 2.8.1.1 Acetoxylation.- 2.8.1.2 Methoxylation.- 2.8.1.3 Formation of Quinones.- 2.8.1.4 Miscellaneous Oxidations.- 2.8.1.5 Oxidation of Benzene.- 2.8.1.6 Acetamidation, Nitration, and Reactions with Pyridine.- 2.8.1.7 Halogenation.- 2.8.1.8 Cyanation.- 2.8.2 Coupling.- 2.8.2.1 Intramolecular Coupling.- 2.8.2.2 Intermolecular Coupling.- 2.8.3 Oxidation at the Benzylic Position.- 2.8.4 Oxidation of Furan, Pyrrole, and Thiophene.- 2.8.4.1 Furans.- 2.8.4.2 Pyrrole and Thiophene.- References.- 2.9 Oxidations Using Mediators.- 2.9.1 Principles.- 2.9.2 Homomediatory Systems.- 2.9.3 Heteromediatory Systems.- 2.9.4 Double Mediatory Systems.- References.- 3 Cathodic Reductions.- 3.1 Cathodic Addition, Substitution, and Coupling.- 3.1.1 Addition.- 3.1.2 Substitution.- 3.1.3 Coupling.- References.- 3.2 Cathodic Eliminations.- 3.2.1 1,1-Elimination.- 3.2.2 1,2-Elimination.- 3.2.3 1,3- and 1,4-Elimination.- 3.2.4 Deprotection.- References.- 3.3 Cathodic Generation of Active Bases.- 3.3.1 Reactions of Electrogenerated Bases.- References.- 1. Constant Current Oxidation.- 2. Controlled Potential Reduction.- 3. Indirect Oxidation Using a Mediator.

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